64024-63-1

Usage

Uses

Used in Pharmaceutical Industry:
4-((Trimethylsilyl)ethynyl)morpholine is used as a synthetic reagent for the modification of the side chain of micromolide, an anti-tuberculosis natural product. Its unique reactivity allows for the efficient functionalization of the side chain, enhancing the drug's efficacy and pharmacological properties.
Used in Antibiotic Synthesis:
In the field of antibiotic development, 4-((Trimethylsilyl)ethynyl)morpholine is employed in the synthesis of antifungal antibiotics (+)-desoxyfugomycin and (+)-fugomycin. 4-((TRIMETHYLSILYL)ETHYNYL)MORPHOLINE plays a crucial role in the sonogashira alkynylation reaction, a widely used method for forming carbon-carbon bonds, which is essential in constructing the complex structures of these antibiotics.
Overall, 4-((Trimethylsilyl)ethynyl)morpholine is a valuable compound in the pharmaceutical industry, particularly for the development and synthesis of novel drugs with improved therapeutic properties. Its unique structure and reactivity make it an essential tool in the synthesis of complex organic molecules, including those with potential applications in the treatment of various diseases.

InChI:InChI=1/C9H17NOSi/c1-12(2,3)9-6-10-4-7-11-8-5-10/h4-5,7-8H2,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 310905-04-5 4-((E)-1,2-Dichloro-vinyl)-morpholine 
• 13306-60-0 N-(trichloroacetyl)morpholine 
• 60506-50-5 1,1,2-Trichloro-2-morpholinoethen 
• 110-91-8 morpholine 
• 7652-06-4 chloroethynyl-trimethyl-silane 

Downstream Products

• 76311-90-5 5-methyl-3-bromo-2(5H)-furanone 
• 1129541-45-2 4-(1-(4-nitrophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-yl)morpholine 
• 1243713-64-5 4-benzyl-5-(4-morpholino-1,3-dithiol-2-ylidene)-6-thioxo-5,6-dihydro[1,2]dithiolo[3,4-b][1,4]thiazin-3(4H)-one 
• 415902-43-1 4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine 

Relevant academic research and scientific papers

A straightforward synthesis of silylated and stannylated ynamines and ynehydrazines

Metallated ynamines 5a-f and ynehydrazines 5g,h were prepared in a very short reaction sequence by consecutive treatment of trichloroethylene (1) with the lithium salt of secondary amines or of trimethylhydrazine, 2 equivalents of butyllithium and chlorotriorganosilanes or -stannanes.

A direct method for the conversion of terminal epoxides into γ-butanolides

A new and efficient process for the conversion of terminal epoxides to γ-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine an

Low-energy pathway for Pauson-Khand reactions: Synthesis and reactivity of dicobalt hexacarbonyl complexes of chiral ynamines

A family of dicobalt hexacarbonyl complexes of 1-(dialkylamino)-2-(trimethysilyl)acetylenes (3a-f) derived both from achiral and chiral amines [a, morpholine; b, (S)-2-methoxymethylpyrrolidine; c, (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine; d, (±)-trans-2,5-bis(benzyloxymethyl)pyrrolidine; e, (2R,5R)-2,5-dimethylpyrrolidine; f, (S)-(α-methylbenzyl)benzylamine] has been prepared by a one-stage process from dichloroacetylene. The methanolysis at room temperature of these complexes (MeOH/K2CO3) induces the selective cleavage of the carbon-silicon bond, leading to the thermally unstable terminal ynamine complexes 12a-f. The Pauson-Khand reaction of 12a-f with strained olefins (norbornadiene and norbornene) takes place at unprecedentedly low temperatures (-35 °C) in the absence of chemical promoters. Diastereoselectivities of up to 94:6 are recorded in these reactions with the ynamine complexes derived from C2 symmetrical chiral auxiliaries (12c,d). The high reactivity depicted by terminal ynamines in the Pauson-Khand reaction has been analyzed by theoretical semiempirical procedures [PM3(tm)] and with density functional theory (VWN/B88), and appears to reflect an easy CO loss from the ynamine-dicobalt hexacarbonyl complexes.

Synthesis of 'push-pull' enynes

'Push-pull' enynes 1a-1f are easily available by Pd catalyzed coupling of stannyl-ynamines 15 and silylynamines 16 with β-iodo-enones 8 (Schemes 7 and 8).